July 8, 2021

7 lessons from starting my first startup


At 19, I started my first startup as a solo founder called Homeroom right after dropping out of college. Bare with me that I am also an immigrant, but that's a story for another day. Homeroom is (was) an educational startup focused on creating connected and data-driven classrooms. Essentially, think of Homeroom as OkCupid and Slack for students and Mixpanel for professors. Through an interface like OkCupid + Slack, students got to engage and feel more connected, while professors utilized the insights (sorta like Mixpanel) to understand student behavior and patterns to better tailor their content to their students.

We conducted multiple pilots in classrooms, but last November (2018), due to a personal/family situation, I had to take a step back from Homeroom. As a 21 year old, I reflect on my 2 years of journey, mistakes I made, lessons I learned, and I thought it was worth sharing to the next 18-19-year-old who dreams of building their own startup one day. As you will notice, these are textbook "What not to do while building a startup 101" and somehow I managed to do it anyways.

These are my opinions from my specific experience. It may or may not apply to everyone.

1) Have a co-founder with you right from the start. 

As a solo founder (and an unexperienced 20-year-old), I thought I could manage everything about a startup, from user interviews to customer outreach to designing to prototyping to developing to everything. While this was manageable, as a result, I was mediocre at everything I did because I couldn't spend time working and focusing on one aspect. When I was building the product, I needed to talk to users, get customers, but when I was spending time talking and attract users for the pilot, I was not building, which made me feel unproductive.

Another important aspect of this and probably the biggest factor/variable for pain & stress in my case is the emotional toll starting a company alone has on you. Not having someone with you to tell you that you’re wrong, to challenge you, to bounce off ideas with, to truly share how you're feeling adds more weight to your shoulders than just building your startup does.

Having a co-founder isn’t only about sharing responsibilities, it's knowing that someone shares your vision for the future and someone that will keep you accountable for what you build because they're just as passionate and vested in the product. In the end, building a great product, startup, and company comes with a big responsibility, and having someone walk abreast with you just makes the startup journey a little less tough.

2) Asking the right questions to your customers/users.

There are three key lessons that I learned, all of which falls under this point. The first one is to talk to your customers/users first. Your idea is a hypothesis and you need to validate this at some point. To do so, talk to your users and ask them questions.

But one thing people don’t tell you is how to ask these questions. For example, I remember having said this in one of the earliest interviews with a professor:

Hi, I am Keshav and I’m working on an educational startup for classrooms called Homeroom. I’m building a product to solidify the relationships between students and teachers to create high engagement in class. Would you want to use something like that in your class?

There are a couple of things wrong with it. I went directly into what Homeroom is, what I am building, with a question to put them in a spot. I was thinking of user interviews as selling my idea to them instead of trying to learning about the problems and challenges they were facing on an everyday basis. The goal of user interviews isn’t to talk about your idea (at least in the beginning)—it's to learn about them, their behavior, how they do things today.

When I asked professors if they would like to use Homeroom for their classes, I put them in spot and most of these professors did not want to be the devil who shuts down a 19-year-old entrepreneur. So guess what they responded with? “Yes, I'll use it.” But when it came time to do so, most of them made excuses and deferred. Instead, I should’ve asked them questions like these:

1. What are the not-so-fun parts of your workflow?

2. What makes it so awful?

3. When was the last time you felt that problem?

4. Can you talk me through the way you’ve tried to fix them? What have yo

While the first two may seem like obvious great questions, the last two are the ones that validate whether or not this problem is real. If the interviewee brings up this "awful" problem, but has done absolutely nothing to fix that, perhaps it isn't that "awful" in the first place. Maybe they just don't give a shit as much. In this case, the goal becomes to find that "awful" problem/part of their workflow until it's validated by something they've done to fix it. If so, try to find this trend in your interview. If this problem surfaces in other interviews, you've got something.

There’s a great book that was recommended to me by a YC alum called “The Mom Test” — the title probably gives it away.

And the final lesson I learned is that talk to ask many people as you can initially. We had about 10 people, but again with the quality of interviews, it didn’t mean anything. 10 good interviews could be enough, but a larger dataset allows you to find patterns in their behaviors, everyday life, and problems.

3) Keep your product's surface area low

This was truly one of the biggest mistakes I made, subconsciously, while working on Homeroom. I knew that my goal is to build the "Most Viable Product" (whatever that means), but I subconsciously started to add new features because infected by the “this would be really cool to have” virus. As I was collecting feedback from students and professors, they said they liked the platform, but adding "x" and "y" and "z" would truly be helpful to them.

As a young founder, I took their words as prophecy and built out those features. By the end of couple of iterations, I had 6-7 features within Homeroom that were quite independent of one another, so by then, I was having a hard time explaining what Homeroom really solved.

You should aim to narrow down and center your solution around one big problem. When building your product, it's temping to add features, especially if your users asked for them, but in most cases, it does more harm than good because at the end you’re left with a product that does many things OK and not one thing extraordinarily. With Homeroom, that was the aftermath—in building out a lot of features, I built a product with no clear tangible value.

A better way to weed out these suggestions is by asking "why?" to your users. Why do you need this feature? If it's something that is a "nice-to-have" but doesn't align with your overall vision, add high product value and get people to pay for it. The first version doesn't need to have 100 features—it just needs to be usable and communicate & add clear value to your end users and potential customers.

Question the intent when someone says "add x" to your product. It may seem easy to build a faster horse, but what you really needed to build is a newer medium for transportation that would revolutionize the way people commute.

Building a product with focus is hard, but what’s even harder is building a product with a lot of features that no one wants to use.

4) The "Startup life" will consume you

There are many trade-offs to building a startup. Yes, you get to work on and build things to improve the lives of others, which is, in and of itself exciting. But building a startup is very time-consuming. There were months where I didn’t speak with my friends or socialize or go out. Even when I really wanted to, there was simply so much to get done that I couldn’t afford to (double true since I was a solo founder).

Working on your startup is a commitment to yourself and your dream. You may find yourself working 70–100 hours a week. You will find yourself thinking only about your startup all the time—when you hang out with friends and family, you'll be thinking about your startup (actually they'll remind you). When you're in the bathroom, you'll be reading blogs by Andrew Chen on growing hacking. When you pitch and get rejected and dejected by your customers, friends, investors, it's going to bother you and keep you up at night.

It's literally like having a baby: it's going to cost you a lot, it's going to require a lot of attention, nurturing, cost you sleepless nights, and unfortunately, some people find themselves being the single mom/dad. Only this time around, "growth" isn't guaranteed.

You're going to feel exhausted, things will not always pan out how you expected them to be, you will be spending the money you saved up, but you're still going to have to keep going. I realized that my social life took a massive hit when I isolated myself as a solo founder. What did I do?

I leveraged Twitter and LinkedIn and reached out to over 250 people in 4 months. I ended up meeting around 50 people and some of the people I've met during this time have become some of my closest friends. They were builders, engineers, designers, product-peeps, former founders, current founders, aspiring founders, investors, angels, and most importantly, people who wanted to do things bigger than themselves.

Being a founder of a company became the reason for me to connect with these people and they gave me advice, insights, and helped me later on in my journey with Homeroom. Even though I didn't have a "co-founder", they provided me with support that I truly needed. Had it not been for running my company, I don't think I would've been able to meet some of the most brilliant people that I did.

5) Be lean and move fast

I’m sure you’re thinking, “Didn't this dude read Lean Startup, Zero to One, and Think & Growth Rich? They all tell you to move fast, get a co-founder, build one thing, etc..” Yes, Yes, and No.

All of these advice seem obvious and were to me until it came time to employ them. I knew that getting a co-founder would be critical, but I couldn't find people that were just as passionate as I was about changing the landscape of classrooms in college. As I alluded, being lean is an advantage for young startups since they can make mistakes, but get up fast, and experiment with things, but being a solo founder slowed me down tremendously. To reduce the friction of speed, I did take some shortcuts like not writing integration tests for user login and everything broke the night before pilot launch. When I fixed the bug, it caused regression in other parts of the codebase. I had no shoulder to cry on.

In the span of 2 years, I spent some of the time on writing business plans, recruiting for co-founders, pitching at competitions/VCs, and planning a kickstarter campaign to raise money for Homeroom (thank god it was just a plan). While I do believe market research/analysis is a crucial step, mapping these financial projections felt like pulling a number out of my ass just to show people that the business is viable. In various competitions, the focus wasn't much on how good a product was—it was on how good your business plan is. But I went along with it because I thought it's just a "startup-y" thing you got to do.

In the retrospect, I wish I had spent more time on analyzing the market thoroughly, talking to customers, building the product, and aggressively got classes and departments to use Homeroom.

6) 9 of 10 startups fail, so just build 10

Ok, so at this point, it may seem like working on my startup was pushing a boulder up a hill and the worst experience ever, right? Nope.

While Homeroom wasn't the success that I had envisioned in the beginning, in no way is it the last one I'll work on. People say "9 out of 10 startups will fail" and to that, I say, "Just build 10, so that at least one can succeed". Sounds ridiculous? No. It's all about mastering your craft.

If you want to be a great software engineer or a great designer or a great marketer, you have to put in the time and be willing to fail. You have to try things even if you know you may be able to achieve them, for the sake of growing, learning, and perfecting your craft.

Building a startup and a company is like that as well. It's the matter of pattern recognition, understanding what works, what doesn't, framing the problem properly, and being cognizant of the value you bring to your customers. These skills develop over time and become instinctual and allow you to be more focused and confident about what you're building and how to get there. So while I am a bit disappointed that Homeroom didn't work out the way I wanted to, I'm glad I got to learn some of these mistakes as a 19 and 20-year-old entrepreneur. To me, that's a better education than sitting in a class.

7) It's about the process

Reid Hoffman puts it interestingly: Building a startup is like jumping off a clip and building an airplane on the way down. While this is pretty extreme, there's some truth to that. The cliff represents stability and jumping is the leap you take trying to build that "next" thing.

Building a startup is about iterating. Most ideas do not strike on the first attempt, which is why you need to always re-assess the product you're building, analyze it from different angles, and determine if there are tweaks you need to make, whether to the product, the targeted demographics, or the market.

In essence, building a startup is a process. In this process, there is a lot of learning, individual growth, failure along the way and a lot of disheartening moments, but when you jumped down from the cliff, you signed up for this. You signed up to be smashed right into the ground. And you might crash a lot of times and that's where intrinsic grit comes into play. You have to have the perseverance to keep getting up and keep moving, whether or not you're with others or alone.

There's a quote from Confucius that has always stuck out to me, which I try to live by:

Our greatest glory is not in never falling, but in rising every time we fall.

So keep falling, keep trying, but keep getting up. I would love to go all cliché right now, but you have your uncle Steve for that. Nevertheless, the point I want to get across is that being smashed into the ground is part of the journey and that building a plane while it's falling isn't always going to work out. If you do it enough times, you must just strike lunch in your 2nd attempt, your 10th attempt or your 14 million-th attempt (just ask Dr. Strange).

In the end, you can't enjoy the fruit of your success and your work unless you have suffered a bit through the disappointments, the failures, the rejections, and the existential crisis along your entrepreneurial journey.

Thanks for reading! For any questions or corrections, please send me an email.
Made with ❤️ in NYC